1680-44-0

Basic information

• Product Name: 5-PHENYL-1H-1,2,3-TRIAZOLE
• Synonyms: 4-Phenyl-1H-1,2,3-triazole;v-Triazole, 4-phenyl-;5-PHENYL-1H-1,2,3-TRIAZOLE;4-Phenyl triazole;4-phenyl-2H-1,2,3-triazole;4-phenyl-2H-triazole
• CAS NO: 1680-44-0
• Molecular Formula: C₈H₇N₃
• Molecular Weight: 145.16
• Product Categories: Heterocyclic Compounds
• Mol File: 1680-44-0.mol

Chemical Properties

• Melting Point: 143-144 °C
• Boiling Point: 346 °C at 760 mmHg
• Flash Point: 169.4 °C
• Appearance: /
• Density: 1.214 g/cm³
• Vapor Pressure: 0.000119mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: 2-8°C
• PKA: 8.40±0.70(Predicted)
• CAS DataBase Reference: 5-PHENYL-1H-1,2,3-TRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYL-1H-1,2,3-TRIAZOLE(1680-44-0)
• EPA Substance Registry System: 5-PHENYL-1H-1,2,3-TRIAZOLE(1680-44-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1680-44-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-PHENYL-1H-1,2,3-TRIAZOLE is utilized as a key intermediate in the synthesis of various organic compounds, leveraging its reactive sites for the formation of new chemical entities.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 5-PHENYL-1H-1,2,3-TRIAZOLE is employed as a building block for the development of new drugs, capitalizing on its structural features to enhance the pharmacological properties of medicinal agents.
Used in Materials Science:
5-PHENYL-1H-1,2,3-TRIAZOLE is used as a component in the design and synthesis of advanced materials, contributing to the creation of novel materials with specific properties for various applications.
Used in Agrochemicals:
5-PHENYL-1H-1,2,3-TRIAZOLE is used as a precursor in the synthesis of agrochemicals, specifically for the development of new pesticides and herbicides, due to its potential to enhance the effectiveness of these products.
Used in Dyes:
In the dye industry, 5-PHENYL-1H-1,2,3-TRIAZOLE is used as a component in the production of dyes, taking advantage of its chemical properties to create dyes with unique color characteristics and improved performance.
Used in Antifungal Applications:
5-PHENYL-1H-1,2,3-TRIAZOLE is investigated for its potential as an antifungal agent, with research studies exploring its ability to inhibit the growth of fungi, offering a new avenue for the development of antifungal treatments.
Used in Anticancer Applications:
In cancer research, 5-PHENYL-1H-1,2,3-TRIAZOLE is being studied for its potential as an anticancer agent, with the aim of identifying its effects on various types of cancer cells and its possible integration into cancer treatment strategies.

InChI:InChI=1/C8H7N3/c1-2-4-7(5-3-1)8-6-9-11-10-8/h1-6H,(H,9,10,11)

Upstream product

• 100-52-7 benzaldehyde 
• 32416-41-4 4-phenyl-1H-1,2,3-triazol-5-amine 
• 536-74-3 phenylacetylene 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 89-92-9 2-methylbenzyl bromide 
• 3958-57-4 1-bromomethyl-3-nitrobenzene 
• 104-81-4 4-Methylbenzyl bromide 
• 1493-27-2 ortho-nitrofluorobenzene 
• 364-74-9 1,4-difluoro-2-nitrobenzene 
• 446-11-7 4-fluoro-3-nitrotoluene 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 2105-96-6 4-fluoro-3-nitrophenol 
• 364-73-8 4-Bromo-1-fluoro-2-nitrobenzene 
• 100-39-0 benzyl bromide 

Downstream Products

• 570387-87-0 2-allyl-4-phenyl-2H-1,2,3-triazole 
• 679842-59-2 1-allyl-4-phenyl-1H-1,2,3-triazole 
• 860653-72-1 2-(2-nitrobenzyl)-4-phenyl-2H-1,2,3-triazole 
• 126800-06-4 1-(2-nitrobenzyl)-4-phenyl-1H-1,2,3-triazole 
• 860653-74-3 1-(2-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole 
• 1268461-16-0 ethyl-4-(4-phenyl-1H-1,2,3-triazol-1-yl)benzoate 

Relevant articles and documents

1, 4-Diazabicyclo[2.2.2]octane-sulfonic acid immobilized on magnetic Fe3O4?SiO2 nanoparticles: a novel and recyclable catalyst for the one-pot synthesis of 4-aryl-NH-1, 2, 3-triazoles

Abstract: In this study, the surface of silica-coated magnetic nanoparticles (Fe3O4?SiO2) were successfully functionalized by an organic ligand of 1, 4-Diazabicyclo[2.2.2]octane (DABCO)-sulfonic acid and used as a highly efficient catalyst for the synthesis of 4-aryl-NH-1, 2, 3-triazoles from the benzyl alcohol derivatives, nitromethane and sodium azide in ethanol. Furthermore, this catalyst could be recovered and reused five times without noticeable loss of activity. Graphic Abstract: Fe3O4?SiO2?TCT-DABCO-SO3H nanoparticles were successfully synthesized and used as a novel, recyclable, efficient and heterogeneous catalyst for the synthesis of 4-aryl-NH-1, 2, 3-triazoles.[Figure not available: see fulltext.]

A Simple Protocol for the Stereoselective Construction of Enaminyl Sulfonyl Fluorides

A clickable connective hub 1-bromo-2-triazolethane-1-sulfonyl fluoride BTESF (1) was developed and successfully applied for the fluorosulfonylvinylation of a host of primary and secondary cyclic or acyclic amines including amino acids and pharmaceuticals. Further antimicrobial experiments revealed that vinyl sulfonyl fluoride functionalized norfloxacin (3ak), ciprofloxacin (3am), and lomefloxacin (3an) exhibited 4-fold improved antimicrobial activity against Gram-positive bacteria compared to their parent drugs.

Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst

In this work, a direct C-H activation of thiophenes was presented via an oxidation pathway under visible-light irradiation, in which the thiophene radical cation serves as the key intermediate. Various thiophenes and azoles could be transformed into the corresponding amination products well, and H2O was the only byproduct which is environmentally benign. Our results showed that tert-butyl nitrite (TBN) served as the electron transfer mediator and O2 as the terminal oxidant to regenerate the photocatalyst DDQ and revive the photocatalytic cycle.

Copper-Catalyzed Three-Component Reaction of Alkynes, TMSN3, and Ethers: Regiocontrollable Synthesis of N1- And N2-Oxyalkylated 1,2,3-Triazoles

A new copper-catalyzed selective synthesis of N1- and N2-oxyalkylated 1,2,3-triazoles has been developed through a three-component reaction of alkynes, TMSN3, and ethers. Through this methodology, a series of N1

Efficient, mild synthesis of N-unsubstituted 1,2,3-triazoles from methanolysis of 1-sulfonyl-1,2,3-triazoles

A small library of diverse N-unsubstituted 1,2,3-triazoles was prepared from the corresponding 1-sulfonyl-1,2,3-triazoles, which were treated only with MeOH at reflux temperature. This process was carried out in good yields showing high efficiency and goo

Recyclable Acid–Base Bifunctional Core–Shell–Shell Nanosphere Catalyzed Synthesis of 5-Aryl-1H-1,2,3-triazoles through the “One-Pot” Cyclization of Aldehydes, Nitromethane, and Sodium Azide

A magnetically separable core–shell–shell nanosphere, Fe3O4@nSiO2-SO3H@MS-NHCOCH3 (n=nonporous, MS=microporous SiO2), was fabricated as an acid–base collaborative catalyst for the three-component cyclization of aromatic aldehydes, nitroalkane, and sodium azide to afford 1H-1,2,3-triazoles. The bifunctional heterogeneous catalyst showed high activity for this transformation and good chemoselectivity, and toxic HN3 was not released during the course of the reaction. A variety of aldehydes were transformed into the corresponding 5-aryl-1H-1,2,3-triazoles in up to 98 % yield. Furthermore, the catalyst could be recovered by using an external magnetic field and reused many times without any loss in activity. In contrast, a homogeneous catalyst system comprising ammonium acetate/acetic acid also worked in this three-component cyclization to afford 1H-1,2,3-triazoles.

Highly Regioselective Radical Transformation of N-Sulfonyl-1,2,3-triazoles in Air

The classic transformations of N-sulfonyl-1,2,3-triazoles were processed via nitrogen anion (hydrolysis, etc.) and carbene intermediates, and no efficient examples via radical intermediates were developed. Here, we reported a catalyst-free radical chain t

SYNTHESIS AND PROPERTIES OF 1,2,3-TRIAZOLES THAT CONTAIN A FERROCENYL RING

Ferrocenesulfonyl azide reacts with a number of aroylmethylenetriphenylphosphinomethylenes in dry methylene chloride to give 1,4,5-trisubstituted 1,2,3-triazoles (61-77percent yields), which are readily converted to 4,5-disubstituted 1,2,3-triazoles and ethyl ferrocenesulfonate when they are refluxed in ethanol.The known triphenylphosphazo ferrocenyl sulfone and ethyl diazoacetate are formed in the case of the reaction of ferrocenesulfonyl azide with carbethoxymethylenetriphenylphosphinomethylene.The structures of the synthesized compounds were proved by the results of elementary analysis and IR, UV, and mass spectroscopy.

Synthesis, DNA-binding abilities and anticancer activities of triazole-pyrrolo[2,1-c][1,4]benzodiazepines hybrid scaffolds

We synthesized a new series of PBD-hybrid derivatives having tethered triazoles and investigated for their cytotoxicity. The studies indicated that cis-olefin compounds induce higher cytotoxicity with increase in the G1 cell cycle phase compared with the trans-compounds. Quantitative RT-PCR assay indicated that compounds (16a-d) induced G1 phase arrest through down-regulation of cyclin D1 and up-regulation of p21, p27, and p53 mRNA expressions. Compounds 16a-d induced A375 early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide. Moreover, the Western blot analysis showed that A375 treated by compounds (16a-d) resulted in decreased levels of Bcl-2 and Bcl-xL, increased levels of Bax and Bad, and caspase/PARP degradation to identify apoptotic cells.

4-Aryl- NH -1,2,3-Triazoles via Multicomponent Reaction of Aldehydes, Nitroalkanes, and Sodium Azide

4-Aryl-NH-1,2,3-triazoles are valuable compounds in organic chemistry and pharmaceutical chemistry. In this paper, we describe a novel multicomponent reaction of aldehydes, nitroalkanes, and sodium azide for the synthesis of 4-aryl-NH-1,2,3-triazoles. In this transformation, it was found that both the slow addition of nitroalkane and the presence of NaHSO3/Na2SO3 are advantageous to promote the reaction results. Additionally, a series of aldehydes and nitro compounds were investigated.